[(2R,3R,4R,5R)-5-(benzoyloxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl benzoate | 492470-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R)-5-(benzoyloxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl benzoate
• CAS: 492470-87-8
• 化学式: C₃₄H₃₂O₇
• 分子量: 552.624
• InChiKey: OUAXINQGCHYISX-SEVDZJIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(benzoyloxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl benzoate 在 草酰氯 、 sodium methylate 、 sodium hydride 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose
  参考文献：
  名称：

  First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

  摘要：

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01760-4
• 作为产物：
  描述：

  溴甲苯 、 2,5-anhydro-1,6-di-O-benzoyl-D-mannitol 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以86%的产率得到[(2R,3R,4R,5R)-5-(benzoyloxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

  摘要：

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01760-4

文献信息

• First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis
  作者：Mukund K. Gurjar、Ravi Nagaprasad、C.V. Ramana

  DOI：10.1016/s0040-4039(02)01760-4

  日期：2002.10

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.